(E)-2,4-Dihydroxy­benzaldehyde 4-ethyl­thio­semicarbazone–4,4′-bipyridine–water (4/7/2)

Ng, S.W.

doi:10.1107/S1600536809030852

organic compounds

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Volume 65| Part 9| September 2009| Page o2129

doi:10.1107/S1600536809030852

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(E)-2,4-Dihydroxybenzaldehyde 4-ethylthiosemicarbazone–4,4′-bipyridine–water (4/7/2)

Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 July 2009; accepted 3 August 2009; online 12 August 2009)

The asymmetric unit of the title compound, 7C₁₀H₈N₂·4C₁₀H₁₃N₃O₂S·2H₂O, contains two independent 2,4-hydroxybenzaldehyde 4-ethylthiosemicarbazone molecules, three and a half 4,4′-bipyridine molecules and one water molecule. Two of the 4,4′-bipyridine molecules lie on general positions and the other three on centers of inversion. The two 4,4′-bipyridine molecules on general positions and one of the three on special positions are disordered over two positions each with an occupancy of 0.50. The –NH—C(=S)—NH—NC fragment is close to planar in the two 2,4-hydroxybenzaldehyde 4-ethylthiosemicarbazone molecules (r.m.s. deviations = 0.04 and 0.05 Å). In the crystal, the Schiff base, N-heterocycle and water molecules engage in O—H⋯O, O—H⋯N and N—H⋯O hydrogen-bonding interactions, generating a layer structure.

Related literature

4,4′-Bipyridine forms a number of clathrates with diphenols; for the quinol clathrate, see: Oswald et al. (2005 ) and for the 2,2′-biphenol clathrate, see: Lavender et al. (1999 ). For the crystal structure of 2,4-dihydroxybenzaldehyde 4-ethylthiosemicarbazone, see: Tan et al. (2008 ).

Experimental

Crystal data

7C₁₀H₈N₂·4C₁₀H₁₃N₃O₂S·2H₂O
M_r = 2086.50
Triclinic, $[P \overline 1]$
a = 11.7683 (3) Å
b = 15.2531 (4) Å
c = 16.0612 (4) Å
α = 74.639 (2)°
β = 86.561 (2)°
γ = 70.252 (1)°
V = 2615.2 (1) Å³
Z = 1
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 153 K
0.20 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.968, T_max = 0.992
18419 measured reflections
10042 independent reflections
6419 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.179
S = 1.02
10042 reflections
686 parameters
170 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N8ⁱ	0.84 (4)	1.92 (1)	2.755 (5)	171 (5)
O1—H1o⋯N8′ⁱ	0.84 (4)	1.97 (1)	2.798 (5)	171 (5)
O2—H2o⋯N7	0.84 (4)	1.93 (1)	2.768 (5)	172 (4)
O2—H2o⋯N7′	0.84 (4)	1.93 (1)	2.766 (5)	178 (4)
O3—H3o⋯N10ⁱⁱ	0.84 (4)	1.91 (1)	2.751 (5)	178 (5)
O3—H3o⋯N10′ⁱⁱ	0.84 (4)	1.90 (1)	2.736 (5)	172 (5)
O4—H4o⋯N11	0.84 (4)	1.90 (1)	2.735 (4)	174 (4)
O1w—H1w1⋯O4	0.84 (3)	2.04 (2)	2.843 (4)	160 (5)
O1w—H1w2⋯N9	0.84 (3)	1.94 (1)	2.782 (5)	175 (7)
O1w—H1w2⋯N9′	0.84 (3)	1.91 (3)	2.722 (5)	160 (7)
N2—H2n⋯O1w	0.88 (3)	1.88 (1)	2.757 (4)	175 (4)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030852/ci2864sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809030852/ci2864Isup2.hkl

checkCIF report

Related literature top

4,4'-Bipyridine forms a number of clathrates with diphenols; for the quinol clathrate, see: Oswald et al. (2005) and for the 2,2'-biphenol clathrate, see: Lavender et al. (1999). For the crystal structure of 2,4-dihydroxybenzaldehyde 4-ethylthiosemicarbazone, see: Tan et al. (2008).

Experimental top

2,4-Dihydroxybenzaldehyde ethylthiosemicarbazone (0.48 g, 2 mmol) and 4,4'-bipyridine (0.15 g, 1 mmol) were dissolved in ethanol (20 ml) and the solution was set aside for a week. The solid material that separated from the solution consisted of small, transparent crystals embedded in some yellow, opaque clumps.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of 7C₁₀H₈N₂.4C₁₀H₁₃N₃O₂S.2H₂O at the 70% probability level; H atoms are drawn as spheres of arbitrary radius. Unlabeled atoms in N11-, N12- and N13-pyridine rings are related to other labeled atoms by the symmetry operation (2 - x, 1 - y, 1 - z), (-x - 1, 2 - y, 1 - z) and (-x, 2 - y, 2 - z), respectively. Only one component of the disordered molecules are shown.

(E)-2,4-Dihydroxybenzaldehyde 4-ethylthiosemicarbazone– 4,4'-bipyridine–water (4/7/2) top

Crystal data top

7(C₁₀H₈N₂)·4(C₁₀H₁₃N₃O₂S)·2(H₂O)	Z = 1
M_r = 2086.50	F(000) = 1098
Triclinic, P1	D_x = 1.325 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.7683 (3) Å	Cell parameters from 3358 reflections
b = 15.2531 (4) Å	θ = 2.6–26.0°
c = 16.0612 (4) Å	µ = 0.16 mm⁻¹
α = 74.639 (2)°	T = 153 K
β = 86.561 (2)°	Plate, yellow
γ = 70.252 (1)°	0.20 × 0.20 × 0.05 mm
V = 2615.2 (1) Å³

Data collection top

Bruker SMART APEX diffractometer	10042 independent reflections
Radiation source: fine-focus sealed tube	6419 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 26.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→15
T_min = 0.968, T_max = 0.992	k = −19→19
18419 measured reflections	l = −20→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.179	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0783P)² + 2.0276P] where P = (F_o² + 2F_c²)/3
10042 reflections	(Δ/σ)_max = 0.001
686 parameters	Δρ_max = 0.66 e Å⁻³
170 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

7(C₁₀H₈N₂)·4(C₁₀H₁₃N₃O₂S)·2(H₂O)	γ = 70.252 (1)°
M_r = 2086.50	V = 2615.2 (1) Å³
Triclinic, P1	Z = 1
a = 11.7683 (3) Å	Mo Kα radiation
b = 15.2531 (4) Å	µ = 0.16 mm⁻¹
c = 16.0612 (4) Å	T = 153 K
α = 74.639 (2)°	0.20 × 0.20 × 0.05 mm
β = 86.561 (2)°

Data collection top

Bruker SMART APEX diffractometer	10042 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6419 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.992	R_int = 0.034
18419 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	170 restraints
wR(F²) = 0.179	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.66 e Å⁻³
10042 reflections	Δρ_min = −0.56 e Å⁻³
686 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.25549 (8)	0.84394 (7)	0.73613 (5)	0.0403 (2)
S2	0.65813 (8)	0.93784 (8)	1.26910 (7)	0.0511 (3)
O1	0.3505 (2)	0.66350 (18)	0.35305 (17)	0.0458 (6)
H1O	0.388 (4)	0.645 (3)	0.311 (2)	0.081 (15)*
O2	−0.0039 (2)	0.74630 (19)	0.17564 (17)	0.0470 (6)
H2O	0.045 (3)	0.721 (3)	0.141 (2)	0.058 (12)*
O3	0.9220 (2)	0.67293 (17)	0.94434 (15)	0.0396 (6)
H3O	0.966 (4)	0.644 (3)	0.910 (3)	0.100 (18)*
O4	0.6292 (2)	0.70169 (17)	0.73457 (14)	0.0386 (5)
H4O	0.693 (2)	0.679 (3)	0.710 (2)	0.066 (13)*
O1w	0.4655 (3)	0.7058 (3)	0.6093 (2)	0.0781 (10)
H1w1	0.500 (4)	0.716 (3)	0.648 (2)	0.078 (16)*
H1w2	0.509 (5)	0.696 (5)	0.567 (3)	0.15 (3)*
N1	0.0466 (2)	0.8843 (2)	0.65301 (18)	0.0353 (6)
H1N	0.008 (3)	0.877 (3)	0.6112 (16)	0.049 (11)*
N2	0.2186 (2)	0.7963 (2)	0.59750 (18)	0.0352 (6)
H2N	0.2980 (10)	0.771 (2)	0.602 (2)	0.049 (11)*
N3	0.1528 (2)	0.79739 (19)	0.52915 (17)	0.0349 (6)
N4	0.4992 (2)	0.91841 (19)	1.17051 (18)	0.0343 (6)
H4N	0.484 (3)	0.904 (3)	1.1236 (14)	0.049 (11)*
N5	0.6981 (2)	0.8472 (2)	1.14649 (18)	0.0381 (7)
H5N	0.7738 (13)	0.839 (2)	1.158 (2)	0.042 (10)*
N6	0.6625 (2)	0.82602 (19)	1.07669 (16)	0.0328 (6)
C1	−0.0538 (3)	0.8798 (3)	0.7937 (2)	0.0504 (10)
H1A	−0.0972	0.9212	0.8308	0.076*
H1B	0.0196	0.8315	0.8244	0.076*
H1C	−0.1057	0.8472	0.7791	0.076*
C2	−0.0201 (3)	0.9405 (2)	0.7120 (2)	0.0417 (8)
H2A	−0.0947	0.9895	0.6818	0.050*
H2B	0.0297	0.9751	0.7275	0.050*
C3	0.1660 (3)	0.8421 (2)	0.6589 (2)	0.0313 (7)
C4	0.2164 (3)	0.7593 (2)	0.4716 (2)	0.0343 (7)
H4	0.3018	0.7335	0.4791	0.041*
C5	0.1601 (3)	0.7548 (2)	0.3954 (2)	0.0335 (7)
C6	0.2295 (3)	0.7075 (2)	0.3359 (2)	0.0362 (8)
C7	0.1760 (3)	0.7045 (2)	0.2625 (2)	0.0372 (8)
H7	0.2243	0.6724	0.2228	0.045*
C8	0.0531 (3)	0.7478 (2)	0.2469 (2)	0.0369 (8)
C9	−0.0184 (3)	0.7960 (2)	0.3044 (2)	0.0382 (8)
H9	−0.1030	0.8264	0.2938	0.046*
C10	0.0360 (3)	0.7987 (2)	0.3766 (2)	0.0371 (8)
H10	−0.0128	0.8318	0.4155	0.045*
C11	0.3731 (3)	0.9035 (3)	1.2993 (2)	0.0487 (9)
H11A	0.3046	0.9408	1.3274	0.073*
H11B	0.4448	0.8770	1.3379	0.073*
H11C	0.3542	0.8507	1.2862	0.073*
C12	0.3977 (3)	0.9690 (2)	1.2159 (2)	0.0384 (8)
H12A	0.3245	0.9965	1.1775	0.046*
H12B	0.4147	1.0232	1.2294	0.046*
C13	0.6134 (3)	0.9001 (2)	1.1925 (2)	0.0345 (7)
C14	0.7464 (3)	0.7858 (2)	1.0308 (2)	0.0318 (7)
H14	0.8286	0.7707	1.0467	0.038*
C15	0.7159 (3)	0.7632 (2)	0.95436 (19)	0.0287 (7)
C16	0.8071 (3)	0.7075 (2)	0.91068 (19)	0.0291 (7)
C17	0.7786 (3)	0.6880 (2)	0.83663 (18)	0.0302 (7)
H17	0.8408	0.6517	0.8065	0.036*
C18	0.6599 (3)	0.7210 (2)	0.80616 (18)	0.0304 (7)
C19	0.5682 (3)	0.7757 (2)	0.8492 (2)	0.0338 (7)
H19	0.4867	0.7987	0.8284	0.041*
C20	0.5975 (3)	0.7958 (2)	0.9220 (2)	0.0322 (7)
H20	0.5349	0.8331	0.9512	0.039*
N7	0.1690 (5)	0.6506 (5)	0.0762 (5)	0.0436 (9)	0.50
C21	0.1857 (6)	0.7027 (3)	−0.0060 (5)	0.0282 (14)	0.50
H21	0.1437	0.7702	−0.0244	0.034*	0.50
C22	0.2638 (7)	0.6562 (5)	−0.0613 (4)	0.0268 (14)	0.50
H22	0.2752	0.6919	−0.1175	0.032*	0.50
C23	0.3253 (5)	0.5576 (5)	−0.0344 (3)	0.0342 (9)	0.50
C24	0.3086 (4)	0.5054 (4)	0.0478 (3)	0.0374 (15)	0.50
H24	0.3506	0.4380	0.0662	0.045*	0.50
C25	0.2304 (5)	0.5519 (4)	0.1031 (3)	0.0419 (15)	0.50
H25	0.2190	0.5163	0.1592	0.050*	0.50
N8	0.5283 (5)	0.4168 (4)	−0.2247 (4)	0.0456 (8)	0.50
C26	0.4775 (4)	0.5168 (4)	−0.2494 (3)	0.0412 (15)	0.50
H26	0.4897	0.5517	−0.3057	0.049*	0.50
C27	0.4088 (4)	0.5656 (3)	−0.1919 (3)	0.0361 (13)	0.50
H27	0.3741	0.6340	−0.2088	0.043*	0.50
C28	0.3910 (5)	0.5145 (5)	−0.1095 (3)	0.0316 (9)	0.50
C29	0.4417 (6)	0.4146 (5)	−0.0848 (4)	0.0283 (14)	0.50
H29	0.4295	0.3796	−0.0285	0.034*	0.50
C30	0.5104 (6)	0.3657 (3)	−0.1423 (5)	0.0322 (15)	0.50
H30	0.5451	0.2974	−0.1254	0.039*	0.50
N7'	0.1582 (5)	0.6579 (5)	0.0664 (5)	0.0436 (9)	0.50
C21'	0.2138 (7)	0.7087 (4)	0.0021 (6)	0.0282 (14)	0.50
H21'	0.1989	0.7753	−0.0039	0.034*	0.50
C22'	0.2911 (6)	0.6620 (5)	−0.0534 (4)	0.0268 (14)	0.50
H22'	0.3291	0.6968	−0.0974	0.032*	0.50
C23'	0.3129 (5)	0.5645 (5)	−0.0447 (4)	0.0342 (9)	0.50
C24'	0.2574 (5)	0.5137 (4)	0.0196 (4)	0.0374 (15)	0.50
H24'	0.2723	0.4471	0.0256	0.045*	0.50
C25'	0.1800 (4)	0.5604 (4)	0.0751 (3)	0.0419 (15)	0.50
H25'	0.1420	0.5257	0.1191	0.050*	0.50
N8'	0.5377 (5)	0.4119 (4)	−0.2166 (5)	0.0456 (8)	0.50
C26'	0.5311 (4)	0.5056 (4)	−0.2200 (3)	0.0412 (15)	0.50
H26'	0.5719	0.5382	−0.2634	0.049*	0.50
C27'	0.4648 (4)	0.5514 (3)	−0.1598 (3)	0.0361 (13)	0.50
H27'	0.4603	0.6154	−0.1621	0.043*	0.50
C28'	0.4051 (5)	0.5037 (5)	−0.0962 (3)	0.0316 (9)	0.50
C29'	0.4117 (6)	0.4101 (5)	−0.0928 (4)	0.0283 (14)	0.50
H29'	0.3709	0.3775	−0.0493	0.034*	0.50
C30'	0.4780 (6)	0.3642 (3)	−0.1530 (5)	0.0322 (15)	0.50
H30'	0.4825	0.3002	−0.1507	0.039*	0.50
N9	0.6183 (5)	0.6645 (4)	0.4755 (3)	0.0440 (18)	0.50
C31	0.6864 (5)	0.7070 (3)	0.4150 (4)	0.0492 (17)	0.50
H31	0.6903	0.7682	0.4152	0.059*	0.50
C32	0.7489 (4)	0.6601 (4)	0.3542 (3)	0.0398 (14)	0.50
H32	0.7954	0.6892	0.3129	0.048*	0.50
C33	0.7432 (5)	0.5706 (4)	0.3540 (4)	0.0336 (12)	0.50
C34	0.6751 (6)	0.5281 (3)	0.4145 (5)	0.0395 (14)	0.50
H34	0.6712	0.4669	0.4143	0.047*	0.50
C35	0.6127 (5)	0.5750 (4)	0.4752 (4)	0.0405 (16)	0.50
H35	0.5661	0.5459	0.5166	0.049*	0.50
N10	0.9335 (5)	0.4261 (4)	0.1649 (3)	0.0391 (8)	0.50
C36	0.8856 (5)	0.5262 (4)	0.1435 (3)	0.0283 (14)	0.50
H36	0.8950	0.5626	0.0871	0.034*	0.50
C37	0.8241 (6)	0.5732 (3)	0.2045 (4)	0.0303 (14)	0.50
H37	0.7914	0.6416	0.1898	0.036*	0.50
C38	0.8105 (5)	0.5199 (3)	0.2869 (4)	0.0314 (10)	0.50
C39	0.8583 (4)	0.4198 (3)	0.3084 (2)	0.0367 (12)	0.50
H39	0.8490	0.3834	0.3648	0.044*	0.50
C40	0.9199 (4)	0.3729 (3)	0.2474 (3)	0.0375 (12)	0.50
H40	0.9526	0.3044	0.2621	0.045*	0.50
N9'	0.6010 (5)	0.6323 (4)	0.4845 (3)	0.0440 (18)	0.50
C31'	0.6291 (5)	0.6924 (3)	0.4109 (4)	0.0492 (17)	0.50
H31'	0.6067	0.7596	0.4057	0.059*	0.50
C32'	0.6898 (5)	0.6541 (4)	0.3448 (3)	0.0398 (14)	0.50
H32'	0.7090	0.6952	0.2945	0.048*	0.50
C33'	0.7225 (6)	0.5558 (4)	0.3525 (4)	0.0336 (12)	0.50
C34'	0.6944 (6)	0.4957 (3)	0.4261 (5)	0.0395 (14)	0.50
H34'	0.7167	0.4285	0.4313	0.047*	0.50
C35'	0.6337 (6)	0.5340 (3)	0.4922 (4)	0.0405 (16)	0.50
H35'	0.6145	0.4929	0.5425	0.049*	0.50
N10'	0.9211 (5)	0.4325 (5)	0.1540 (3)	0.0391 (8)	0.50
C36'	0.9193 (5)	0.5226 (4)	0.1589 (3)	0.0283 (14)	0.50
H36'	0.9624	0.5566	0.1187	0.034*	0.50
C37'	0.8547 (6)	0.5630 (3)	0.2227 (4)	0.0303 (14)	0.50
H37'	0.8535	0.6246	0.2260	0.036*	0.50
C38'	0.7917 (5)	0.5134 (4)	0.2815 (4)	0.0314 (10)	0.50
C39'	0.7934 (4)	0.4233 (3)	0.2767 (3)	0.0367 (12)	0.50
H39'	0.7504	0.3894	0.3169	0.044*	0.50
C40'	0.8581 (4)	0.3829 (3)	0.2129 (3)	0.0375 (12)	0.50
H40'	0.8593	0.3213	0.2096	0.045*	0.50
N11	0.8292 (4)	0.6185 (4)	0.6505 (3)	0.0392 (10)	0.50
C41	0.9111 (4)	0.6576 (3)	0.6025 (3)	0.0398 (12)	0.50
H41	0.9174	0.7158	0.6092	0.048*	0.50
C42	0.9836 (4)	0.6115 (3)	0.5446 (3)	0.0398 (12)	0.50
H42	1.0395	0.6382	0.5118	0.048*	0.50
C43	0.9743 (5)	0.5263 (3)	0.5348 (3)	0.0299 (11)	0.50
C44	0.8924 (5)	0.4872 (3)	0.5828 (4)	0.0270 (14)	0.50
H44	0.8861	0.4290	0.5761	0.032*	0.50
C45	0.8199 (5)	0.5334 (4)	0.6407 (3)	0.0289 (14)	0.50
H45	0.7640	0.5067	0.6735	0.035*	0.50
N11'	0.8058 (5)	0.6149 (4)	0.6454 (3)	0.0392 (10)	0.50
C41'	0.8322 (4)	0.6690 (3)	0.5672 (3)	0.0398 (12)	0.50
H41'	0.8013	0.7375	0.5535	0.048*	0.50
C42'	0.9038 (4)	0.6229 (3)	0.5089 (2)	0.0398 (12)	0.50
H42'	0.9218	0.6599	0.4555	0.048*	0.50
C43'	0.9490 (5)	0.5228 (3)	0.5289 (3)	0.0299 (11)	0.50
C44'	0.9227 (5)	0.4687 (3)	0.6071 (4)	0.0270 (14)	0.50
H44'	0.9536	0.4002	0.6207	0.032*	0.50
C45'	0.8511 (5)	0.5147 (4)	0.6653 (3)	0.0289 (14)	0.50
H45'	0.8330	0.4777	0.7188	0.035*	0.50
N12	−0.1892 (2)	0.9088 (2)	0.56896 (19)	0.0413 (7)
C46	−0.2279 (3)	0.9691 (2)	0.4914 (2)	0.0421 (8)
H46	−0.1695	0.9873	0.4538	0.050*
C47	−0.3472 (3)	1.0070 (2)	0.4621 (2)	0.0392 (8)
H47	−0.3688	1.0504	0.4064	0.047*
C48	−0.4356 (3)	0.9812 (2)	0.51455 (19)	0.0306 (7)
C49	−0.3957 (3)	0.9185 (2)	0.5956 (2)	0.0389 (8)
H49	−0.4518	0.8986	0.6344	0.047*
C50	−0.2754 (3)	0.8854 (2)	0.6193 (2)	0.0424 (8)
H50	−0.2515	0.8431	0.6752	0.051*
N13	0.3191 (3)	0.8864 (2)	1.0389 (2)	0.0523 (8)
C51	0.2705 (4)	0.9350 (3)	0.9600 (3)	0.0574 (11)
H51	0.3237	0.9394	0.9135	0.069*
C52	0.1478 (3)	0.9795 (3)	0.9415 (2)	0.0518 (10)
H52	0.1192	1.0120	0.8837	0.062*
C53	0.0666 (3)	0.9762 (2)	1.0080 (2)	0.0371 (8)
C54	0.1158 (3)	0.9245 (2)	1.0897 (2)	0.0417 (8)
H54	0.0647	0.9185	1.1374	0.050*
C55	0.2396 (3)	0.8816 (3)	1.1015 (2)	0.0479 (9)
H55	0.2704	0.8462	1.1583	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0363 (5)	0.0501 (5)	0.0309 (4)	−0.0126 (4)	0.0032 (4)	−0.0077 (4)
S2	0.0350 (5)	0.0713 (7)	0.0654 (6)	−0.0167 (5)	0.0108 (4)	−0.0514 (6)
O1	0.0297 (13)	0.0553 (15)	0.0630 (17)	−0.0139 (11)	0.0150 (12)	−0.0363 (14)
O2	0.0386 (14)	0.0649 (17)	0.0536 (16)	−0.0230 (13)	0.0166 (12)	−0.0379 (14)
O3	0.0308 (13)	0.0503 (14)	0.0357 (13)	−0.0050 (11)	0.0080 (10)	−0.0203 (11)
O4	0.0421 (14)	0.0454 (14)	0.0293 (12)	−0.0104 (11)	0.0074 (11)	−0.0181 (11)
O1w	0.0499 (17)	0.119 (3)	0.0486 (17)	0.0148 (16)	−0.0045 (14)	−0.0489 (18)
N1	0.0298 (15)	0.0382 (15)	0.0381 (16)	−0.0083 (12)	0.0068 (12)	−0.0155 (13)
N2	0.0273 (15)	0.0398 (16)	0.0415 (16)	−0.0101 (13)	0.0082 (13)	−0.0184 (13)
N3	0.0344 (15)	0.0342 (15)	0.0413 (16)	−0.0155 (12)	0.0108 (13)	−0.0152 (12)
N4	0.0313 (15)	0.0362 (15)	0.0380 (16)	−0.0069 (12)	0.0050 (12)	−0.0202 (13)
N5	0.0276 (15)	0.0537 (18)	0.0433 (16)	−0.0146 (14)	0.0090 (13)	−0.0302 (14)
N6	0.0349 (15)	0.0376 (15)	0.0318 (14)	−0.0140 (12)	0.0082 (12)	−0.0180 (12)
C1	0.049 (2)	0.050 (2)	0.056 (2)	−0.0161 (18)	0.0219 (19)	−0.0252 (19)
C2	0.0370 (19)	0.0362 (18)	0.053 (2)	−0.0072 (15)	0.0079 (16)	−0.0210 (16)
C3	0.0333 (17)	0.0275 (16)	0.0330 (17)	−0.0116 (13)	0.0083 (14)	−0.0077 (13)
C4	0.0281 (16)	0.0324 (17)	0.0469 (19)	−0.0127 (14)	0.0117 (15)	−0.0165 (15)
C5	0.0312 (17)	0.0316 (16)	0.0450 (19)	−0.0164 (14)	0.0145 (15)	−0.0169 (15)
C6	0.0297 (17)	0.0357 (18)	0.054 (2)	−0.0185 (14)	0.0170 (15)	−0.0222 (16)
C7	0.0340 (18)	0.0379 (18)	0.052 (2)	−0.0184 (15)	0.0189 (16)	−0.0266 (16)
C8	0.0322 (18)	0.0412 (19)	0.049 (2)	−0.0210 (15)	0.0143 (15)	−0.0221 (16)
C9	0.0296 (17)	0.0421 (19)	0.050 (2)	−0.0160 (15)	0.0116 (15)	−0.0213 (16)
C10	0.0342 (18)	0.0355 (18)	0.049 (2)	−0.0144 (15)	0.0177 (15)	−0.0229 (16)
C11	0.044 (2)	0.054 (2)	0.054 (2)	−0.0196 (18)	0.0175 (18)	−0.0236 (19)
C12	0.0279 (17)	0.0398 (19)	0.047 (2)	−0.0040 (14)	0.0074 (15)	−0.0218 (16)
C13	0.0311 (18)	0.0344 (17)	0.0412 (18)	−0.0124 (14)	0.0120 (14)	−0.0157 (15)
C14	0.0295 (16)	0.0340 (17)	0.0360 (17)	−0.0129 (14)	0.0096 (14)	−0.0146 (14)
C15	0.0322 (17)	0.0278 (15)	0.0276 (16)	−0.0114 (13)	0.0086 (13)	−0.0096 (13)
C16	0.0280 (16)	0.0273 (15)	0.0298 (16)	−0.0087 (13)	0.0087 (13)	−0.0063 (13)
C17	0.0347 (17)	0.0282 (16)	0.0251 (16)	−0.0073 (13)	0.0108 (13)	−0.0089 (13)
C18	0.0398 (18)	0.0288 (16)	0.0223 (15)	−0.0128 (14)	0.0074 (13)	−0.0059 (13)
C19	0.0321 (17)	0.0368 (18)	0.0304 (17)	−0.0095 (14)	0.0037 (14)	−0.0084 (14)
C20	0.0332 (17)	0.0287 (16)	0.0320 (17)	−0.0060 (13)	0.0102 (14)	−0.0114 (13)
N7	0.0465 (19)	0.051 (2)	0.040 (2)	−0.0195 (16)	0.0131 (16)	−0.0216 (17)
C21	0.029 (3)	0.0387 (19)	0.031 (2)	−0.0195 (18)	−0.007 (2)	−0.0192 (16)
C22	0.029 (3)	0.0328 (18)	0.0305 (19)	−0.0228 (19)	0.000 (2)	−0.0115 (16)
C23	0.0334 (19)	0.0347 (18)	0.037 (2)	−0.0138 (15)	0.0092 (16)	−0.0115 (16)
C24	0.038 (3)	0.036 (2)	0.038 (3)	−0.012 (2)	0.009 (2)	−0.010 (2)
C25	0.039 (3)	0.049 (2)	0.041 (3)	−0.020 (3)	0.008 (2)	−0.011 (2)
N8	0.0305 (17)	0.0496 (19)	0.059 (2)	−0.0095 (14)	0.0123 (15)	−0.0260 (17)
C26	0.035 (3)	0.050 (2)	0.046 (3)	−0.019 (3)	0.014 (2)	−0.020 (2)
C27	0.036 (3)	0.035 (2)	0.039 (3)	−0.013 (2)	0.009 (2)	−0.011 (2)
C28	0.0282 (19)	0.031 (2)	0.034 (2)	−0.0096 (16)	0.0049 (16)	−0.0064 (17)
C29	0.022 (3)	0.0336 (18)	0.0334 (19)	−0.0144 (19)	−0.004 (2)	−0.0079 (16)
C30	0.021 (4)	0.0358 (18)	0.043 (3)	−0.0053 (18)	−0.012 (2)	−0.0167 (17)
N7'	0.0465 (19)	0.051 (2)	0.040 (2)	−0.0195 (16)	0.0131 (16)	−0.0216 (17)
C21'	0.029 (3)	0.0387 (19)	0.031 (2)	−0.0195 (18)	−0.007 (2)	−0.0192 (16)
C22'	0.029 (3)	0.0328 (18)	0.0305 (19)	−0.0228 (19)	0.000 (2)	−0.0115 (16)
C23'	0.0334 (19)	0.0347 (18)	0.037 (2)	−0.0138 (15)	0.0092 (16)	−0.0115 (16)
C24'	0.038 (3)	0.036 (2)	0.038 (3)	−0.012 (2)	0.009 (2)	−0.010 (2)
C25'	0.039 (3)	0.049 (2)	0.041 (3)	−0.020 (3)	0.008 (2)	−0.011 (2)
N8'	0.0305 (17)	0.0496 (19)	0.059 (2)	−0.0095 (14)	0.0123 (15)	−0.0260 (17)
C26'	0.035 (3)	0.050 (2)	0.046 (3)	−0.019 (3)	0.014 (2)	−0.020 (2)
C27'	0.036 (3)	0.035 (2)	0.039 (3)	−0.013 (2)	0.009 (2)	−0.011 (2)
C28'	0.0282 (19)	0.031 (2)	0.034 (2)	−0.0096 (16)	0.0049 (16)	−0.0064 (17)
C29'	0.022 (3)	0.0336 (18)	0.0334 (19)	−0.0144 (19)	−0.004 (2)	−0.0079 (16)
C30'	0.021 (4)	0.0358 (18)	0.043 (3)	−0.0053 (18)	−0.012 (2)	−0.0167 (17)
N9	0.040 (3)	0.050 (5)	0.037 (2)	−0.005 (3)	0.0048 (17)	−0.017 (3)
C31	0.053 (4)	0.046 (3)	0.040 (2)	−0.002 (3)	0.000 (3)	−0.017 (2)
C32	0.044 (4)	0.036 (2)	0.034 (2)	−0.006 (2)	0.005 (3)	−0.0093 (18)
C33	0.031 (2)	0.034 (2)	0.0305 (16)	−0.0044 (16)	0.0036 (16)	−0.0078 (15)
C34	0.038 (3)	0.041 (3)	0.036 (2)	−0.008 (3)	0.009 (2)	−0.012 (3)
C35	0.035 (3)	0.044 (4)	0.037 (3)	−0.006 (3)	0.005 (2)	−0.012 (3)
N10	0.0273 (17)	0.0492 (19)	0.0391 (18)	−0.0054 (14)	0.0060 (14)	−0.0194 (16)
C36	0.014 (3)	0.043 (2)	0.026 (2)	−0.006 (2)	−0.008 (2)	−0.0083 (18)
C37	0.025 (3)	0.0354 (19)	0.027 (3)	−0.0045 (19)	−0.005 (2)	−0.0084 (18)
C38	0.028 (2)	0.0308 (18)	0.0309 (18)	−0.0036 (16)	0.0038 (16)	−0.0097 (15)
C39	0.038 (3)	0.037 (2)	0.035 (2)	−0.012 (2)	0.0079 (19)	−0.0095 (18)
C40	0.037 (3)	0.036 (2)	0.038 (3)	−0.007 (2)	0.002 (2)	−0.015 (2)
N9'	0.040 (3)	0.050 (5)	0.037 (2)	−0.005 (3)	0.0048 (17)	−0.017 (3)
C31'	0.053 (4)	0.046 (3)	0.040 (2)	−0.002 (3)	0.000 (3)	−0.017 (2)
C32'	0.044 (4)	0.036 (2)	0.034 (2)	−0.006 (2)	0.005 (3)	−0.0093 (18)
C33'	0.031 (2)	0.034 (2)	0.0305 (16)	−0.0044 (16)	0.0036 (16)	−0.0078 (15)
C34'	0.038 (3)	0.041 (3)	0.036 (2)	−0.008 (3)	0.009 (2)	−0.012 (3)
C35'	0.035 (3)	0.044 (4)	0.037 (3)	−0.006 (3)	0.005 (2)	−0.012 (3)
N10'	0.0273 (17)	0.0492 (19)	0.0391 (18)	−0.0054 (14)	0.0060 (14)	−0.0194 (16)
C36'	0.014 (3)	0.043 (2)	0.026 (2)	−0.006 (2)	−0.008 (2)	−0.0083 (18)
C37'	0.025 (3)	0.0354 (19)	0.027 (3)	−0.0045 (19)	−0.005 (2)	−0.0084 (18)
C38'	0.028 (2)	0.0308 (18)	0.0309 (18)	−0.0036 (16)	0.0038 (16)	−0.0097 (15)
C39'	0.038 (3)	0.037 (2)	0.035 (2)	−0.012 (2)	0.0079 (19)	−0.0095 (18)
C40'	0.037 (3)	0.036 (2)	0.038 (3)	−0.007 (2)	0.002 (2)	−0.015 (2)
N11	0.039 (2)	0.0432 (18)	0.0345 (16)	−0.0080 (16)	0.0083 (16)	−0.0186 (14)
C41	0.048 (3)	0.038 (2)	0.037 (3)	−0.012 (2)	0.004 (2)	−0.018 (2)
C42	0.042 (3)	0.035 (2)	0.040 (3)	−0.011 (2)	0.015 (2)	−0.011 (2)
C43	0.034 (3)	0.0284 (17)	0.0249 (17)	−0.0060 (17)	0.0060 (18)	−0.0089 (14)
C44	0.026 (3)	0.031 (2)	0.022 (3)	−0.007 (2)	−0.002 (2)	−0.007 (2)
C45	0.024 (3)	0.040 (3)	0.019 (3)	−0.006 (2)	−0.005 (2)	−0.007 (2)
N11'	0.039 (2)	0.0432 (18)	0.0345 (16)	−0.0080 (16)	0.0083 (16)	−0.0186 (14)
C41'	0.048 (3)	0.038 (2)	0.037 (3)	−0.012 (2)	0.004 (2)	−0.018 (2)
C42'	0.042 (3)	0.035 (2)	0.040 (3)	−0.011 (2)	0.015 (2)	−0.011 (2)
C43'	0.034 (3)	0.0284 (17)	0.0249 (17)	−0.0060 (17)	0.0060 (18)	−0.0089 (14)
C44'	0.026 (3)	0.031 (2)	0.022 (3)	−0.007 (2)	−0.002 (2)	−0.007 (2)
C45'	0.024 (3)	0.040 (3)	0.019 (3)	−0.006 (2)	−0.005 (2)	−0.007 (2)
N12	0.0373 (16)	0.0340 (15)	0.0480 (17)	−0.0078 (13)	0.0078 (13)	−0.0100 (14)
C46	0.040 (2)	0.0369 (19)	0.046 (2)	−0.0140 (16)	0.0115 (16)	−0.0058 (16)
C47	0.0399 (19)	0.0386 (19)	0.0350 (18)	−0.0133 (15)	0.0096 (15)	−0.0046 (15)
C48	0.0381 (17)	0.0237 (15)	0.0291 (16)	−0.0082 (13)	0.0102 (14)	−0.0101 (13)
C49	0.040 (2)	0.0306 (17)	0.0397 (19)	−0.0101 (15)	0.0097 (15)	−0.0031 (15)
C50	0.045 (2)	0.0338 (18)	0.0377 (19)	−0.0054 (16)	0.0063 (16)	−0.0023 (15)
N13	0.0445 (18)	0.0436 (18)	0.058 (2)	−0.0058 (15)	−0.0058 (16)	−0.0050 (16)
C51	0.047 (2)	0.049 (2)	0.059 (3)	−0.0063 (19)	0.009 (2)	−0.002 (2)
C52	0.048 (2)	0.048 (2)	0.042 (2)	−0.0030 (18)	−0.0010 (17)	−0.0004 (17)
C53	0.0438 (19)	0.0246 (16)	0.0378 (18)	−0.0048 (14)	−0.0017 (15)	−0.0076 (14)
C54	0.045 (2)	0.0373 (19)	0.0386 (19)	−0.0060 (16)	0.0005 (16)	−0.0135 (16)
C55	0.051 (2)	0.043 (2)	0.042 (2)	−0.0086 (18)	−0.0096 (18)	−0.0064 (17)

Geometric parameters (Å, º) top

S1—C3	1.686 (3)	C26'—C27'	1.39
S2—C13	1.667 (3)	C26'—H26'	0.95
O1—C6	1.363 (4)	C27'—C28'	1.39
O1—H1O	0.84 (4)	C27'—H27'	0.95
O2—C8	1.370 (4)	C28'—C29'	1.39
O2—H2O	0.84 (4)	C29'—C30'	1.39
O3—C16	1.361 (4)	C29'—H29'	0.95
O3—H3O	0.84 (4)	C30'—H30'	0.95
O4—C18	1.357 (4)	N9—C31	1.39
O4—H4O	0.84 (4)	N9—C35	1.39
O1w—H1w1	0.84 (3)	C31—C32	1.39
O1w—H1w2	0.84 (3)	C31—H31	0.95
N1—C3	1.331 (4)	C32—C33	1.39
N1—C2	1.461 (4)	C32—H32	0.95
N1—H1N	0.88 (3)	C33—C34	1.39
N2—C3	1.357 (4)	C33—C38	1.520 (5)
N2—N3	1.374 (4)	C34—C35	1.39
N2—H2N	0.88 (3)	C34—H34	0.95
N3—C4	1.288 (4)	C35—H35	0.95
N4—C13	1.327 (4)	N10—C36	1.39
N4—C12	1.458 (4)	N10—C40	1.39
N4—H4N	0.88 (3)	C36—C37	1.39
N5—C13	1.369 (4)	C36—H36	0.95
N5—N6	1.370 (4)	C37—C38	1.39
N5—H5N	0.88 (3)	C37—H37	0.95
N6—C14	1.280 (4)	C38—C39	1.39
C1—C2	1.510 (5)	C39—C40	1.39
C1—H1A	0.98	C39—H39	0.95
C1—H1B	0.98	C40—H40	0.95
C1—H1C	0.98	N9'—C31'	1.39
C2—H2A	0.99	N9'—C35'	1.39
C2—H2B	0.99	C31'—C32'	1.39
C4—C5	1.454 (5)	C31'—H31'	0.95
C4—H4	0.95	C32'—C33'	1.39
C5—C10	1.398 (5)	C32'—H32'	0.95
C5—C6	1.405 (4)	C33'—C34'	1.39
C6—C7	1.388 (5)	C33'—C38'	1.517 (5)
C7—C8	1.379 (4)	C34'—C35'	1.39
C7—H7	0.95	C34'—H34'	0.95
C8—C9	1.396 (4)	C35'—H35'	0.95
C9—C10	1.375 (5)	N10'—C36'	1.39
C9—H9	0.95	N10'—C40'	1.39
C10—H10	0.95	C36'—C37'	1.39
C11—C12	1.521 (5)	C36'—H36'	0.95
C11—H11A	0.98	C37'—C38'	1.39
C11—H11B	0.98	C37'—H37'	0.95
C11—H11C	0.98	C38'—C39'	1.39
C12—H12A	0.99	C39'—C40'	1.39
C12—H12B	0.99	C39'—H39'	0.95
C14—C15	1.455 (4)	C40'—H40'	0.95
C14—H14	0.95	N11—C41	1.39
C15—C20	1.393 (4)	N11—C45	1.39
C15—C16	1.405 (4)	C41—C42	1.39
C16—C17	1.385 (4)	C41—H41	0.95
C17—C18	1.385 (4)	C42—C43	1.39
C17—H17	0.95	C42—H42	0.95
C18—C19	1.395 (4)	C43—C44	1.39
C19—C20	1.376 (4)	C43—C43ⁱ	1.525 (8)
C19—H19	0.95	C44—C45	1.39
C20—H20	0.95	C44—H44	0.95
N7—C21	1.39	C45—H45	0.95
N7—C25	1.39	N11'—C41'	1.39
C21—C22	1.39	N11'—C45'	1.39
C21—H21	0.95	C41'—C42'	1.39
C22—C23	1.39	C41'—H41'	0.95
C22—H22	0.95	C42'—C43'	1.39
C23—C24	1.39	C42'—H42'	0.95
C23—C28	1.565 (6)	C43'—C44'	1.39
C24—C25	1.39	C43'—C43'ⁱ	1.558 (8)
C24—H24	0.95	C44'—C45'	1.39
C25—H25	0.95	C44'—H44'	0.95
N8—C26	1.39	C45'—H45'	0.95
N8—C30	1.39	N12—C46	1.336 (4)
C26—C27	1.39	N12—C50	1.343 (4)
C26—H26	0.95	C46—C47	1.384 (5)
C27—C28	1.39	C46—H46	0.95
C27—H27	0.95	C47—C48	1.394 (4)
C28—C29	1.39	C47—H47	0.95
C29—C30	1.39	C48—C49	1.392 (4)
C29—H29	0.95	C48—C48ⁱⁱ	1.484 (6)
C30—H30	0.95	C49—C50	1.373 (5)
N7'—C21'	1.39	C49—H49	0.95
N7'—C25'	1.39	C50—H50	0.95
C21'—C22'	1.39	N13—C51	1.335 (5)
C21'—H21'	0.95	N13—C55	1.337 (5)
C22'—C23'	1.39	C51—C52	1.384 (5)
C22'—H22'	0.95	C51—H51	0.95
C23'—C24'	1.39	C52—C53	1.392 (5)
C23'—C28'	1.530 (6)	C52—H52	0.95
C24'—C25'	1.39	C53—C54	1.383 (5)
C24'—H24'	0.95	C53—C53ⁱⁱⁱ	1.494 (7)
C25'—H25'	0.95	C54—C55	1.381 (5)
N8'—C26'	1.39	C54—H54	0.95
N8'—C30'	1.39	C55—H55	0.95

C6—O1—H1O	113 (3)	N8'—C26'—H26'	120.0
C8—O2—H2O	113 (3)	C26'—C27'—C28'	120.0
C16—O3—H3O	106 (4)	C26'—C27'—H27'	120.0
C18—O4—H4O	108 (3)	C28'—C27'—H27'	120.0
H1w1—O1w—H1w2	114 (5)	C29'—C28'—C27'	120.0
C3—N1—C2	122.8 (3)	C29'—C28'—C23'	121.6 (5)
C3—N1—H1N	117 (2)	C27'—C28'—C23'	117.1 (5)
C2—N1—H1N	120 (2)	C28'—C29'—C30'	120.0
C3—N2—N3	121.8 (3)	C28'—C29'—H29'	120.0
C3—N2—H2N	115 (2)	C30'—C29'—H29'	120.0
N3—N2—H2N	123 (2)	C29'—C30'—N8'	120.0
C4—N3—N2	114.8 (3)	C29'—C30'—H30'	120.0
C13—N4—C12	122.8 (3)	N8'—C30'—H30'	120.0
C13—N4—H4N	119 (2)	C31—N9—C35	120.0
C12—N4—H4N	118 (2)	C32—C31—N9	120.0
C13—N5—N6	119.8 (3)	C32—C31—H31	120.0
C13—N5—H5N	116 (2)	N9—C31—H31	120.0
N6—N5—H5N	123 (2)	C31—C32—C33	120.0
C14—N6—N5	116.7 (3)	C31—C32—H32	120.0
C2—C1—H1A	109.5	C33—C32—H32	120.0
C2—C1—H1B	109.5	C32—C33—C34	120.0
H1A—C1—H1B	109.5	C32—C33—C38	119.9 (4)
C2—C1—H1C	109.5	C34—C33—C38	120.1 (4)
H1A—C1—H1C	109.5	C33—C34—C35	120.0
H1B—C1—H1C	109.5	C33—C34—H34	120.0
N1—C2—C1	113.3 (3)	C35—C34—H34	120.0
N1—C2—H2A	108.9	C34—C35—N9	120.0
C1—C2—H2A	108.9	C34—C35—H35	120.0
N1—C2—H2B	108.9	N9—C35—H35	120.0
C1—C2—H2B	108.9	C36—N10—C40	120.0
H2A—C2—H2B	107.7	N10—C36—C37	120.0
N1—C3—N2	117.4 (3)	N10—C36—H36	120.0
N1—C3—S1	124.2 (2)	C37—C36—H36	120.0
N2—C3—S1	118.4 (2)	C36—C37—C38	120.0
N3—C4—C5	121.4 (3)	C36—C37—H37	120.0
N3—C4—H4	119.3	C38—C37—H37	120.0
C5—C4—H4	119.3	C39—C38—C37	120.0
C10—C5—C6	116.9 (3)	C39—C38—C33	119.7 (4)
C10—C5—C4	122.2 (3)	C37—C38—C33	120.3 (4)
C6—C5—C4	120.9 (3)	C38—C39—C40	120.0
O1—C6—C7	121.0 (3)	C38—C39—H39	120.0
O1—C6—C5	118.1 (3)	C40—C39—H39	120.0
C7—C6—C5	120.9 (3)	C39—C40—N10	120.0
C8—C7—C6	120.3 (3)	C39—C40—H40	120.0
C8—C7—H7	119.9	N10—C40—H40	120.0
C6—C7—H7	119.9	C31'—N9'—C35'	120.0
O2—C8—C7	122.4 (3)	C32'—C31'—N9'	120.0
O2—C8—C9	117.3 (3)	C32'—C31'—H31'	120.0
C7—C8—C9	120.3 (3)	N9'—C31'—H31'	120.0
C10—C9—C8	118.7 (3)	C31'—C32'—C33'	120.0
C10—C9—H9	120.6	C31'—C32'—H32'	120.0
C8—C9—H9	120.6	C33'—C32'—H32'	120.0
C9—C10—C5	122.9 (3)	C32'—C33'—C34'	120.0
C9—C10—H10	118.6	C32'—C33'—C38'	120.1 (4)
C5—C10—H10	118.6	C34'—C33'—C38'	119.9 (4)
C12—C11—H11A	109.5	C35'—C34'—C33'	120.0
C12—C11—H11B	109.5	C35'—C34'—H34'	120.0
H11A—C11—H11B	109.5	C33'—C34'—H34'	120.0
C12—C11—H11C	109.5	C34'—C35'—N9'	120.0
H11A—C11—H11C	109.5	C34'—C35'—H35'	120.0
H11B—C11—H11C	109.5	N9'—C35'—H35'	120.0
N4—C12—C11	112.5 (3)	C36'—N10'—C40'	120.0
N4—C12—H12A	109.1	N10'—C36'—C37'	120.0
C11—C12—H12A	109.1	N10'—C36'—H36'	120.0
N4—C12—H12B	109.1	C37'—C36'—H36'	120.0
C11—C12—H12B	109.1	C38'—C37'—C36'	120.0
H12A—C12—H12B	107.8	C38'—C37'—H37'	120.0
N4—C13—N5	115.5 (3)	C36'—C37'—H37'	120.0
N4—C13—S2	124.9 (2)	C37'—C38'—C39'	120.0
N5—C13—S2	119.5 (2)	C37'—C38'—C33'	120.6 (4)
N6—C14—C15	120.0 (3)	C39'—C38'—C33'	119.4 (4)
N6—C14—H14	120.0	C40'—C39'—C38'	120.0
C15—C14—H14	120.0	C40'—C39'—H39'	120.0
C20—C15—C16	118.2 (3)	C38'—C39'—H39'	120.0
C20—C15—C14	121.8 (3)	C39'—C40'—N10'	120.0
C16—C15—C14	120.1 (3)	C39'—C40'—H40'	120.0
O3—C16—C17	122.0 (3)	N10'—C40'—H40'	120.0
O3—C16—C15	117.9 (3)	C41—N11—C45	120.0
C17—C16—C15	120.1 (3)	N11—C41—C42	120.0
C16—C17—C18	120.5 (3)	N11—C41—H41	120.0
C16—C17—H17	119.8	C42—C41—H41	120.0
C18—C17—H17	119.8	C41—C42—C43	120.0
O4—C18—C17	121.7 (3)	C41—C42—H42	120.0
O4—C18—C19	118.1 (3)	C43—C42—H42	120.0
C17—C18—C19	120.2 (3)	C44—C43—C42	120.0
C20—C19—C18	119.0 (3)	C44—C43—C43ⁱ	109.9 (7)
C20—C19—H19	120.5	C42—C43—C43ⁱ	129.1 (7)
C18—C19—H19	120.5	C45—C44—C43	120.0
C19—C20—C15	122.1 (3)	C45—C44—H44	120.0
C19—C20—H20	118.9	C43—C44—H44	120.0
C15—C20—H20	118.9	C44—C45—N11	120.0
C21—N7—C25	120.0	C44—C45—H45	120.0
N7—C21—C22	120.0	N11—C45—H45	120.0
N7—C21—H21	120.0	C41'—N11'—C45'	120.0
C22—C21—H21	120.0	C42'—C41'—N11'	120.0
C21—C22—C23	120.0	C42'—C41'—H41'	120.0
C21—C22—H22	120.0	N11'—C41'—H41'	120.0
C23—C22—H22	120.0	C41'—C42'—C43'	120.0
C24—C23—C22	120.0	C41'—C42'—H42'	120.0
C24—C23—C28	126.3 (5)	C43'—C42'—H42'	120.0
C22—C23—C28	112.9 (5)	C42'—C43'—C44'	120.0
C25—C24—C23	120.0	C42'—C43'—C43'ⁱ	116.6 (6)
C25—C24—H24	120.0	C44'—C43'—C43'ⁱ	122.0 (6)
C23—C24—H24	120.0	C43'—C44'—C45'	120.0
C24—C25—N7	120.0	C43'—C44'—H44'	120.0
C24—C25—H25	120.0	C45'—C44'—H44'	120.0
N7—C25—H25	120.0	C44'—C45'—N11'	120.0
C26—N8—C30	120.0	C44'—C45'—H45'	120.0
C27—C26—N8	120.0	N11'—C45'—H45'	120.0
C27—C26—H26	120.0	C46—N12—C50	115.3 (3)
N8—C26—H26	120.0	N12—C46—C47	124.4 (3)
C26—C27—C28	120.0	N12—C46—H46	117.8
C26—C27—H27	120.0	C47—C46—H46	117.8
C28—C27—H27	120.0	C46—C47—C48	119.7 (3)
C29—C28—C27	120.0	C46—C47—H47	120.1
C29—C28—C23	112.9 (5)	C48—C47—H47	120.1
C27—C28—C23	126.9 (5)	C49—C48—C47	116.0 (3)
C28—C29—C30	120.0	C49—C48—C48ⁱⁱ	122.3 (3)
C28—C29—H29	120.0	C47—C48—C48ⁱⁱ	121.7 (3)
C30—C29—H29	120.0	C50—C49—C48	120.0 (3)
C29—C30—N8	120.0	C50—C49—H49	120.0
C29—C30—H30	120.0	C48—C49—H49	120.0
N8—C30—H30	120.0	N12—C50—C49	124.5 (3)
C21'—N7'—C25'	120.0	N12—C50—H50	117.7
C22'—C21'—N7'	120.0	C49—C50—H50	117.7
C22'—C21'—H21'	120.0	C51—N13—C55	115.0 (3)
N7'—C21'—H21'	120.0	N13—C51—C52	124.5 (4)
C21'—C22'—C23'	120.0	N13—C51—H51	117.7
C21'—C22'—H22'	120.0	C52—C51—H51	117.7
C23'—C22'—H22'	120.0	C51—C52—C53	119.7 (3)
C24'—C23'—C22'	120.0	C51—C52—H52	120.2
C24'—C23'—C28'	115.3 (5)	C53—C52—H52	120.2
C22'—C23'—C28'	124.5 (5)	C54—C53—C52	116.3 (3)
C23'—C24'—C25'	120.0	C54—C53—C53ⁱⁱⁱ	121.7 (4)
C23'—C24'—H24'	120.0	C52—C53—C53ⁱⁱⁱ	122.0 (4)
C25'—C24'—H24'	120.0	C55—C54—C53	119.7 (3)
C24'—C25'—N7'	120.0	C55—C54—H54	120.2
C24'—C25'—H25'	120.0	C53—C54—H54	120.2
N7'—C25'—H25'	120.0	N13—C55—C54	124.8 (3)
C26'—N8'—C30'	120.0	N13—C55—H55	117.6
C27'—C26'—N8'	120.0	C54—C55—H55	117.6
C27'—C26'—H26'	120.0

C3—N2—N3—C4	173.4 (3)	C24'—C23'—C28'—C27'	−178.5 (3)
C13—N5—N6—C14	172.5 (3)	C22'—C23'—C28'—C27'	−4.4 (6)
C3—N1—C2—C1	−86.2 (4)	C27'—C28'—C29'—C30'	0.0
C2—N1—C3—N2	−176.4 (3)	C23'—C28'—C29'—C30'	166.7 (6)
C2—N1—C3—S1	2.2 (4)	C28'—C29'—C30'—N8'	0.0
N3—N2—C3—N1	3.3 (4)	C26'—N8'—C30'—C29'	0.0
N3—N2—C3—S1	−175.4 (2)	C35—N9—C31—C32	0.0
N2—N3—C4—C5	180.0 (3)	N9—C31—C32—C33	0.0
N3—C4—C5—C10	5.7 (5)	C31—C32—C33—C34	0.0
N3—C4—C5—C6	−175.8 (3)	C31—C32—C33—C38	179.4 (6)
C10—C5—C6—O1	−179.5 (3)	C32—C33—C34—C35	0.0
C4—C5—C6—O1	1.9 (4)	C38—C33—C34—C35	−179.4 (6)
C10—C5—C6—C7	−0.4 (5)	C33—C34—C35—N9	0.0
C4—C5—C6—C7	−179.0 (3)	C31—N9—C35—C34	0.0
O1—C6—C7—C8	178.8 (3)	C40—N10—C36—C37	0.0
C5—C6—C7—C8	−0.2 (5)	N10—C36—C37—C38	0.0
C6—C7—C8—O2	−179.6 (3)	C36—C37—C38—C39	0.0
C6—C7—C8—C9	0.7 (5)	C36—C37—C38—C33	−179.9 (6)
O2—C8—C9—C10	179.9 (3)	C32—C33—C38—C39	146.9 (4)
C7—C8—C9—C10	−0.4 (5)	C34—C33—C38—C39	−33.7 (6)
C8—C9—C10—C5	−0.3 (5)	C32—C33—C38—C37	−33.2 (6)
C6—C5—C10—C9	0.7 (5)	C34—C33—C38—C37	146.2 (3)
C4—C5—C10—C9	179.3 (3)	C37—C38—C39—C40	0.0
C13—N4—C12—C11	−80.2 (4)	C33—C38—C39—C40	179.9 (6)
C12—N4—C13—N5	176.5 (3)	C38—C39—C40—N10	0.0
C12—N4—C13—S2	−4.5 (5)	C36—N10—C40—C39	0.0
N6—N5—C13—N4	7.0 (4)	C35'—N9'—C31'—C32'	0.0
N6—N5—C13—S2	−172.1 (2)	N9'—C31'—C32'—C33'	0.0
N5—N6—C14—C15	−178.4 (3)	C31'—C32'—C33'—C34'	0.0
N6—C14—C15—C20	9.0 (5)	C31'—C32'—C33'—C38'	−178.4 (6)
N6—C14—C15—C16	−171.3 (3)	C32'—C33'—C34'—C35'	0.0
C20—C15—C16—O3	−177.7 (3)	C38'—C33'—C34'—C35'	178.4 (6)
C14—C15—C16—O3	2.7 (4)	C33'—C34'—C35'—N9'	0.0
C20—C15—C16—C17	1.3 (4)	C31'—N9'—C35'—C34'	0.0
C14—C15—C16—C17	−178.4 (3)	C40'—N10'—C36'—C37'	0.0
O3—C16—C17—C18	177.3 (3)	N10'—C36'—C37'—C38'	0.0
C15—C16—C17—C18	−1.6 (4)	C36'—C37'—C38'—C39'	0.0
C16—C17—C18—O4	−179.0 (3)	C36'—C37'—C38'—C33'	178.9 (6)
C16—C17—C18—C19	1.0 (4)	C32'—C33'—C38'—C37'	19.7 (7)
O4—C18—C19—C20	179.8 (3)	C34'—C33'—C38'—C37'	−158.7 (3)
C17—C18—C19—C20	−0.2 (4)	C32'—C33'—C38'—C39'	−161.4 (4)
C18—C19—C20—C15	−0.1 (5)	C34'—C33'—C38'—C39'	20.3 (6)
C16—C15—C20—C19	−0.4 (4)	C37'—C38'—C39'—C40'	0.0
C14—C15—C20—C19	179.2 (3)	C33'—C38'—C39'—C40'	−178.9 (6)
C25—N7—C21—C22	0.0	C38'—C39'—C40'—N10'	0.0
N7—C21—C22—C23	0.0	C36'—N10'—C40'—C39'	0.0
C21—C22—C23—C24	0.0	C45—N11—C41—C42	0.0
C21—C22—C23—C28	170.0 (5)	N11—C41—C42—C43	0.0
C22—C23—C24—C25	0.0	C41—C42—C43—C44	0.0
C28—C23—C24—C25	−168.5 (6)	C41—C42—C43—C43ⁱ	167.5 (10)
C23—C24—C25—N7	0.0	C42—C43—C44—C45	0.0
C21—N7—C25—C24	0.0	C43ⁱ—C43—C44—C45	−169.7 (8)
C30—N8—C26—C27	0.0	C43—C44—C45—N11	0.0
N8—C26—C27—C28	0.0	C41—N11—C45—C44	0.0
C26—C27—C28—C29	0.0	C45'—N11'—C41'—C42'	0.0
C26—C27—C28—C23	174.9 (6)	N11'—C41'—C42'—C43'	0.0
C24—C23—C28—C29	−4.5 (6)	C41'—C42'—C43'—C44'	0.0
C22—C23—C28—C29	−173.7 (3)	C41'—C42'—C43'—C43'ⁱ	−166.4 (9)
C24—C23—C28—C27	−179.7 (3)	C42'—C43'—C44'—C45'	0.0
C22—C23—C28—C27	11.1 (6)	C43'ⁱ—C43'—C44'—C45'	165.6 (10)
C27—C28—C29—C30	0.0	C43'—C44'—C45'—N11'	0.0
C23—C28—C29—C30	−175.6 (5)	C41'—N11'—C45'—C44'	0.0
C28—C29—C30—N8	0.0	C50—N12—C46—C47	0.1 (5)
C26—N8—C30—C29	0.0	N12—C46—C47—C48	−0.9 (5)
C25'—N7'—C21'—C22'	0.0	C46—C47—C48—C49	1.0 (5)
N7'—C21'—C22'—C23'	0.0	C46—C47—C48—C48ⁱⁱ	−179.2 (4)
C21'—C22'—C23'—C24'	0.0	C47—C48—C49—C50	−0.4 (5)
C21'—C22'—C23'—C28'	−173.9 (6)	C48ⁱⁱ—C48—C49—C50	179.8 (4)
C22'—C23'—C24'—C25'	0.0	C46—N12—C50—C49	0.5 (5)
C28'—C23'—C24'—C25'	174.5 (5)	C48—C49—C50—N12	−0.4 (5)
C23'—C24'—C25'—N7'	0.0	C55—N13—C51—C52	0.8 (6)
C21'—N7'—C25'—C24'	0.0	N13—C51—C52—C53	1.1 (7)
C30'—N8'—C26'—C27'	0.0	C51—C52—C53—C54	−2.2 (5)
N8'—C26'—C27'—C28'	0.0	C51—C52—C53—C53ⁱⁱⁱ	179.3 (4)
C26'—C27'—C28'—C29'	0.0	C52—C53—C54—C55	1.4 (5)
C26'—C27'—C28'—C23'	−167.3 (5)	C53ⁱⁱⁱ—C53—C54—C55	179.9 (4)
C24'—C23'—C28'—C29'	14.4 (6)	C51—N13—C55—C54	−1.7 (6)
C22'—C23'—C28'—C29'	−171.4 (4)	C53—C54—C55—N13	0.5 (6)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x−1, −y+2, −z+1; (iii) −x, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N8^iv	0.84 (4)	1.92 (1)	2.755 (5)	171 (5)
O1—H1o···N8′^iv	0.84 (4)	1.97 (1)	2.798 (5)	171 (5)
O2—H2o···N7	0.84 (4)	1.93 (1)	2.768 (5)	172 (4)
O2—H2o···N7′	0.84 (4)	1.93 (1)	2.766 (5)	178 (4)
O3—H3o···N10ⁱ	0.84 (4)	1.91 (1)	2.751 (5)	178 (5)
O3—H3o···N10′ⁱ	0.84 (4)	1.90 (1)	2.736 (5)	172 (5)
O4—H4o···N11	0.84 (4)	1.90 (1)	2.735 (4)	174 (4)
O1w—H1w1···O4	0.84 (3)	2.04 (2)	2.843 (4)	160 (5)
O1w—H1w2···N9	0.84 (3)	1.94 (1)	2.782 (5)	175 (7)
O1w—H1w2···N9′	0.84 (3)	1.91 (3)	2.722 (5)	160 (7)
N1—H1n···N12	0.88 (3)	2.31 (3)	3.024 (4)	138 (3)
N2—H2n···O1w	0.88 (3)	1.88 (1)	2.757 (4)	175 (4)
N4—H4n···N13	0.88 (3)	2.56 (2)	3.315 (4)	144 (3)
N5—H5n···O2^v	0.88 (1)	2.51 (2)	3.325 (4)	155 (3)

Symmetry codes: (i) −x+2, −y+1, −z+1; (iv) −x+1, −y+1, −z; (v) x+1, y, z+1.

Experimental details

Crystal data
Chemical formula	7(C₁₀H₈N₂)·4(C₁₀H₁₃N₃O₂S)·2(H₂O)
M_r	2086.50
Crystal system, space group	Triclinic, P1
Temperature (K)	153
a, b, c (Å)	11.7683 (3), 15.2531 (4), 16.0612 (4)
α, β, γ (°)	74.639 (2), 86.561 (2), 70.252 (1)
V (Å³)	2615.2 (1)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.20 × 0.20 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.968, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	18419, 10042, 6419
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.179, 1.02
No. of reflections	10042
No. of parameters	686
No. of restraints	170
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.56

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N8ⁱ	0.84 (4)	1.92 (1)	2.755 (5)	171 (5)
O1—H1o···N8'ⁱ	0.84 (4)	1.97 (1)	2.798 (5)	171 (5)
O2—H2o···N7	0.84 (4)	1.93 (1)	2.768 (5)	172 (4)
O2—H2o···N7'	0.84 (4)	1.93 (1)	2.766 (5)	178 (4)
O3—H3o···N10ⁱⁱ	0.84 (4)	1.91 (1)	2.751 (5)	178 (5)
O3—H3o···N10'ⁱⁱ	0.84 (4)	1.90 (1)	2.736 (5)	172 (5)
O4—H4o···N11	0.84 (4)	1.90 (1)	2.735 (4)	174 (4)
O1w—H1w1···O4	0.84 (3)	2.04 (2)	2.843 (4)	160 (5)
O1w—H1w2···N9	0.84 (3)	1.94 (1)	2.782 (5)	175 (7)
O1w—H1w2···N9'	0.84 (3)	1.91 (3)	2.722 (5)	160 (7)
N2—H2n···O1w	0.88 (3)	1.88 (1)	2.757 (4)	175 (4)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y+1, −z+1.

Acknowledgements

The author thanks the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lavender, E. S., Ferguson, G. & Glidewell, C. (1999). Acta Cryst. C55, 430–432. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Oswald, I. D. H., Motherwell, W. D. S. & Parsons, S. (2005). Acta Cryst. B61, 46–57. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tan, K. W., Ng, C. H., Maah, M. J. & Ng, S. W. (2008). Acta Cryst. E64, o2123. Web of Science CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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Volume 65| Part 9| September 2009| Page o2129

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-2,4-Di­hydroxy­benzaldehyde 4-ethyl­thio­semicarbazone–4,4′-bi­pyridine–water (4/7/2)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-2,4-Dihydroxybenzaldehyde 4-ethylthiosemicarbazone–4,4′-bipyridine–water (4/7/2)